Pd-catalyzed intramolecular amidation of 2-(buta-1,3-dienyl)phenylcarbamoyl chloride: a concise synthesis of spiro[indoline-3,3′-pyrrolidine]

A palladium-catalyzed intramolecular amidation of arylcarbamic acid derivatives bearing 1,3-diene moiety with or without external nucleophiles is described. The tandem cycloamidation and nucleophilic allylic substitution are successfully applied to the construction of the spiro[indoline-3,3'-pyrrolidine] skeleton as well as contiguous stereogenic centers with an aim of synthesizing spirocyclic oxindole alkaloids. (C) 2009 Elsevier Ltd. All rights reserved.